Reported is the synthesis of azo mutual prodrugs of the nonsteroidal anti-inflammatory agents (NSAIDs) 4-aminophenylacetic acid (4-APAA) or 5-aminosalicylic acid (5-ASA) with peptides, including an antibiotic peptide temporin analogue modified at the amino terminal by an α-aminoisobutyric acid (Aib) residue. These prodrugs are designed for colonic delivery of two agents to treat infection and inflammation by the bacterial pathogen Clostridium difficile .

Key indicatorsSingle-crystal X-ray study T = 100 K Mean '(C±C) = 0.003 A Ê R factor = 0.049 wR factor = 0.128 Data-to-parameter ratio = 12.6For details of how these key indicators were automatically derived from the article, see

Key indicatorsSingle-crystal X-ray study T = 100 K Mean '(C±C) = 0.003 A Ê R factor = 0.072 wR factor = 0.155 Data-to-parameter ratio = 12.5For details of how these key indicators were automatically derived from the article, see

Key indicatorsSingle-crystal X-ray study T = 173 K Mean (C-C) = 0.005 Å R factor = 0.067 wR factor = 0.177 Data-to-parameter ratio = 20.9For details of how these key indicators were automatically derived from the article, see

Within and between mol­ecules of the title compound, C7H11N2+·C6H5NO3−·C6H4NO3, there are C—H⋯O, C—H⋯N, O—H⋯O and N—H⋯O interactions, which generate rings of graph‐set motifs S(5), R12(5), R12(6), R12(7) and R21(4). The supramolecular aggregation is completed by the presence of three different π–π interactions and short van der Waals contacts.